scholarly journals Merging the Versatile Functionalities of Boronic Acid with Peptides

2021 ◽  
Vol 22 (23) ◽  
pp. 12958
Author(s):  
Yahong Tan ◽  
Junjie Wu ◽  
Lulu Song ◽  
Mengmeng Zhang ◽  
Christopher John Hipolito ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Enzyme Inhibitors ◽  
Biological Activities ◽  
Boronic Acids ◽  
Peptide Ligands ◽  
Water Soluble ◽  
Ph Responsive ◽  
Peptide Cyclization ◽  
Starting Point ◽  
Bacterial Surfaces

Peptides inherently feature the favorable properties of being easily synthesized, water-soluble, biocompatible, and typically non-toxic. Thus, boronic acid has been widely integrated with peptides with the goal of discovering peptide ligands with novel biological activities, and this effort has led to broad applications. Taking the integration between boronic acid and peptide as a starting point, we provide an overview of the latest research advances and highlight the versatile and robust functionalities of boronic acid. In this review, we summarize the diverse applications of peptide boronic acids in medicinal chemistry and chemical biology, including the identification of covalent reversible enzyme inhibitors, recognition, and detection of glycans on proteins or cancer cell surface, delivery of siRNAs, development of pH responsive devices, and recognition of RNA or bacterial surfaces. Additionally, we discuss boronic acid-mediated peptide cyclization and peptide modifications, as well as the facile chemical synthesis of peptide boronic acids, which paved the way for developing a growing number of peptide boronic acids.

scholarly journals A Theoretical Model to Study the Interaction Between Boronic Acids and Insulin

2020 ◽  
Author(s):  
Durgesh Kumar ◽  
Kamlesh Kumari ◽  
PRASHANT SINGH
Keyword(s):  
Amino Acids ◽  
Theoretical Model ◽  
Boronic Acid ◽  
Significant Interaction ◽  
Biological Activities ◽  
Boronic Acids ◽  
Biological Molecules ◽  
Computational Tools ◽  
Medical Expertise ◽  
Stabilizing Agents

Boronic acids are widely used in various applications in view of their ability to recognize and bind at specific sites of the biological molecules to mimic several processes. Therefore, this has attracted the researchers, academician and medical expertise to explore them. In the present work, the authors have designed a theoretical approach to study the interaction of boronic acid with insulin using computational tools. A library of boronic acids (114 compounds) are designed, optimized and interacted with insulin using computational tools i.e. iGEMDOCK. Further, their different biological activities and toxicity are determined. Results indicates the promising potential of the boronic acids on interaction with the insulin. Amongst, 114 molecules of boronic acids, 3-Benzyloxyphenylboronic acid (71) showed the best interaction with amino-acids of insulin and significant interaction was shown with the Glu21 and His5 residues. Further, these results were compared with the stabilizing agents and found to be more potent.

scholarly journals A Theoretical Model to Study the Interaction Between Boronic Acids and Insulin

2020 ◽  
Author(s):  
Durgesh Kumar ◽  
Kamlesh Kumari ◽  
PRASHANT SINGH
Keyword(s):  
Amino Acids ◽  
Theoretical Model ◽  
Boronic Acid ◽  
Significant Interaction ◽  
Biological Activities ◽  
Boronic Acids ◽  
Biological Molecules ◽  
Computational Tools ◽  
Medical Expertise ◽  
Stabilizing Agents

Boronic acids are widely used in various applications in view of their ability to recognize and bind at specific sites of the biological molecules to mimic several processes. Therefore, this has attracted the researchers, academician and medical expertise to explore them. In the present work, the authors have designed a theoretical approach to study the interaction of boronic acid with insulin using computational tools. A library of boronic acids (114 compounds) are designed, optimized and interacted with insulin using computational tools i.e. iGEMDOCK. Further, their different biological activities and toxicity are determined. Results indicates the promising potential of the boronic acids on interaction with the insulin. Amongst, 114 molecules of boronic acids, 3-Benzyloxyphenylboronic acid (71) showed the best interaction with amino-acids of insulin and significant interaction was shown with the Glu21 and His5 residues. Further, these results were compared with the stabilizing agents and found to be more potent.

scholarly journals New Insights into the Stereochemical Requirements of the Bombesin BB1 Receptor Antagonists Binding

2020 ◽  
Vol 13 (8) ◽  
pp. 197
Author(s):  
Bahareh Rasaeifar ◽  
Patricia Gomez-Gutierrez ◽  
Juan J. Perez
Keyword(s):  
Biological Activities ◽  
Docking Study ◽  
Experimental Information ◽  
Peptide Ligands ◽  
Peripheral Tissues ◽  
Starting Point ◽  
Wide Range ◽  
The Family ◽  
The Central Nervous System ◽  
G Protein Coupled

Members of the family of bombesinlike peptides exert a wide range of biological activities both at the central nervous system and in peripheral tissues through at least three G-Protein Coupled Receptors: BB1, BB2 and BB3. Despite the number of peptide ligands already described, only a few small molecule binders have been disclosed so far, hampering a deeper understanding of their pharmacology. In order to have a deeper understanding of the stereochemical features characterizing binding to the BB1 receptor, we performed the molecular modeling study consisting of the construction of a 3D model of the receptor by homology modeling followed by a docking study of the peptoids PD168368 and PD176252 onto it. Analysis of the complexes permitted us to propose prospective bound conformations of the compounds, consistent with the experimental information available. Subsequently, we defined a pharmacophore describing minimal stereochemical requirements for binding to the BB1 receptor that was used in silico screening. This exercise yielded a set of small molecules that were purchased and tested, showing affinity to the BB1 but not to the BB2 receptor. These molecules exhibit scaffolds of diverse chemical families that can be used as a starting point for the development of novel BB1 antagonists.

A common mechanism links activities of butyrate in the colon

2017 ◽  
Author(s):  
Mohit S. Verma ◽  
Michael J. Fink ◽  
Gabriel L Salmon ◽  
Nadine Fornelos ◽  
Takahiro E. Ohara ◽  
...  
Keyword(s):  
Stem Cells ◽  
Histone Deacetylases ◽  
Biological Activities ◽  
Short Chain Fatty Acids ◽  
Common Mechanism ◽  
Epithelial Stem Cells ◽  
Degree Of Unsaturation ◽  
Structure Activity ◽  
Starting Point ◽  
New Compounds

Two biological activities of butyrate in the colon (suppression of proliferation of colonic epithelial stem cells and inflammation) correlate with inhibition of histone deacetylases. Cellular and biochemical studies of molecules similar in structure to butyrate, but different in molecular details (functional groups, chain-length, deuteration, oxidation level, fluorination, or degree of unsaturation) demonstrated that these activities were sensitive to molecular structure, and were compatible with the hypothesis that butyrate acts by binding to the Zn<sup>2+</sup> in the catalytic site of histone deacetylases. Structure-activity relationships drawn from a set of 36 compounds offer a starting point for the design of new compounds targeting the inhibition of histone deacetylases. The observation that butyrate was more potent than other short-chain fatty acids is compatible with the hypothesis that crypts evolved (at least in part), to separate stem cells at the base of crypts from butyrate produced by commensal bacteria.

Chalcones: As potent α-amylase enzyme inhibitors; synthesis, in vitro, and in silico studies

2020 ◽  
Vol 16 ◽  
Author(s):  
Mahboob Ali ◽  
Momin Khan ◽  
Khair Zaman ◽  
Abdul Wadood ◽  
Maryam Iqbal ◽  
...  
Keyword(s):  
In Silico ◽  
Enzyme Inhibitors ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Type Ii Diabetes Mellitus ◽  
Spectroscopic Techniques ◽  
Chalcone Derivatives ◽  
In Silico Studies ◽  
Wide Range

: Background: The inhibition of α-amylase enzyme is one of the best therapeutic approach for the management of type II diabetes mellitus. Chalcone possesses a wide range of biological activities. Objective: In the current study chalcone derivatives (1-17) were synthesized and evaluated their inhibitory potential against α-amylase enzyme. Method: For that purpose, a library of substituted (E)-1-(naphthalene-2-yl)-3-phenylprop-2-en-1-ones was synthesized by ClaisenSchmidt condensation reaction of 2-acetonaphthanone and substituted aryl benzaldehyde in the presence of base and characterized via different spectroscopic techniques such as EI-MS, HREI-MS, 1H-, and 13C-NMR. Results: Sixteen synthetic chalcones were evaluated for in vitro porcine pancreatic α-amylase inhibition. All the chalcones demonstrated good inhibitory activities in the range of IC50 = 1.25 ± 1.05 to 2.40 ± 0.09 μM as compared to the standard commercial drug acarbose (IC50 = 1.34 ± 0.3 μM). Conclusion: Chalcone derivatives (1-17) were synthesized, characterized, and evaluated for their α-amylase inhibition. SAR revealed that electron donating groups in the phenyl ring have more influence on enzyme inhibition. However, to insight the participation of different substituents in the chalcones on the binding interactions with the α-amylase enzyme, in silico (computer simulation) molecular modeling analyses were carried out.

scholarly journals Natural Molecules and Neuroprotection: Kynurenic Acid, Pantethine and α-Lipoic Acid

2021 ◽  
Vol 22 (1) ◽  
pp. 403
Author(s):  
Fanni Tóth ◽  
Edina Katalin Cseh ◽  
László Vécsei
Keyword(s):  
Neurodegenerative Diseases ◽  
Lipoic Acid ◽  
Kynurenic Acid ◽  
Biological Activities ◽  
Neuroprotective Effect ◽  
Structural Diversity ◽  
Kynurenine Pathway ◽  
Glutamate Excitotoxicity ◽  
Neuroprotective Agents ◽  
Starting Point

The incidence of neurodegenerative diseases has increased greatly worldwide due to the rise in life expectancy. In spite of notable development in the understanding of these disorders, there has been limited success in the development of neuroprotective agents that can slow the progression of the disease and prevent neuronal death. Some natural products and molecules are very promising neuroprotective agents because of their structural diversity and wide variety of biological activities. In addition to their neuroprotective effect, they are known for their antioxidant, anti-inflammatory and antiapoptotic effects and often serve as a starting point for drug discovery. In this review, the following natural molecules are discussed: firstly, kynurenic acid, the main neuroprotective agent formed via the kynurenine pathway of tryptophan metabolism, as it is known mainly for its role in glutamate excitotoxicity, secondly, the dietary supplement pantethine, that is many sided, well tolerated and safe, and the third molecule, α-lipoic acid is a universal antioxidant. As a conclusion, because of their beneficial properties, these molecules are potential candidates for neuroprotective therapies suitable in managing neurodegenerative diseases.

Grafting pH‐Responsive Copolymers to Cold Water‐Soluble Starch Using Nitroxide‐Mediated Polymerization

2021 ◽  
pp. 2100011
Author(s):  
Alexander T. Fritz ◽  
Jaime C. Cazotti ◽  
Omar Garcia‐Valdez ◽  
Niels M. B. Smeets ◽  
Marc A. Dubé ◽  
...  
Keyword(s):  
Cold Water ◽  
Soluble Starch ◽  
Water Soluble ◽  
Ph Responsive ◽  
Nitroxide Mediated Polymerization

scholarly journals Phytochemical Composition and Biological Activities of Scorzonera Species

2021 ◽  
Vol 22 (10) ◽  
pp. 5128
Author(s):  
Karolina Lendzion ◽  
Agnieszka Gornowicz ◽  
Krzysztof Bielawski ◽  
Anna Bielawska
Keyword(s):  
Biological Activities ◽  
Folk Medicine ◽  
Quinic Acid ◽  
Hepatoprotective Activity ◽  
Phytochemical Composition ◽  
Starting Point ◽  
Microbial Infections ◽  
Bacteria And Fungi ◽  
Bioactive Potential

The genus Scorzonera comprises nearly 200 species, naturally occurring in Europe, Asia, and northern parts of Africa. Plants belonging to the Scorzonera genus have been a significant part of folk medicine in Asia, especially China, Mongolia, and Turkey for centuries. Therefore, they have become the subject of research regarding their phytochemical composition and biological activity. The aim of this review is to present and assess the phytochemical composition, and bioactive potential of species within the genus Scorzonera. Studies have shown the presence of many bioactive compounds like triterpenoids, sesquiterpenoids, flavonoids, or caffeic acid and quinic acid derivatives in extracts obtained from aerial and subaerial parts of the plants. The antioxidant and cytotoxic properties have been evaluated, together with the mechanism of anti-inflammatory, analgesic, and hepatoprotective activity. Scorzonera species have also been investigated for their activity against several bacteria and fungi strains. Despite mild cytotoxicity against cancer cell lines in vitro, the bioactive properties in wound healing therapy and the treatment of microbial infections might, in perspective, be the starting point for the research on Scorzonera species as active agents in medical products designed for miscellaneous skin conditions.

scholarly journals Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3224
Author(s):  
Leander Geske ◽  
Ulrich Kauhl ◽  
Mohamed E. M. Saeed ◽  
Anja Schüffler ◽  
Eckhard Thines ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Biological Evaluation ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Total Syntheses ◽  
Wittig Olefination ◽  
Starting Point ◽  
Perkin Reaction ◽  
Synthesis And Biological Evaluation

The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.

scholarly journals Analyzing the Carotenoid Composition of Melilot (Melilotus officinalis (L.) Pall.) Extracts and the Effects of Isolated (All-E)-lutein-5,6-epoxide on Primary Sensory Neurons and Macrophages

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 503
Author(s):  
Györgyi Horváth ◽  
Eszter Csikós ◽  
Eichertné Violetta Andres ◽  
Tímea Bencsik ◽  
Anikó Takátsy ◽  
...  
Keyword(s):  
Liquid Chromatography ◽  
Sensory Neurons ◽  
Biological Activities ◽  
Water Soluble ◽  
Soluble Form ◽  
Primary Sensory Neurons ◽  
Isolation And Identification ◽  
Melilotus Officinalis ◽  
Carotenoid Composition ◽  
Anti Inflammatory

Melilotus officinalis is known to contain several types of secondary metabolites. In contrast, the carotenoid composition of this medicinal plant has not been investigated, although it may also contribute to the biological activities of the drug, such as anti-inflammatory effects. Therefore, this study focuses on the isolation and identification of carotenoids from Meliloti herba and on the effect of isolated (all-E)-lutein 5,6-epoxide on primary sensory neurons and macrophages involved in nociception, as well as neurogenic and non-neurogenic inflammatory processes. The composition of the plant extracts was analyzed by high performance liquid chromatography (HPLC). The main carotenoid was isolated by column liquid chromatography (CLC) and identified by MS and NMR. The effect of water-soluble lutein 5,6-epoxide-RAMEB (randomly methylated-β-cyclodextrin) was investigated on Ca2+-influx in rat primary sensory neurons induced by the activation of the transient receptor potential ankyrin 1 receptor agonist to mustard-oil and on endotoxin-induced IL-1β release from isolated mouse peritoneal macrophages. (all-E)-Lutein 5,6-epoxide significantly decreased the percent of responsive primary sensory neurons compared to the vehicle-treated stimulated control. Furthermore, endotoxin-evoked IL-1β release from macrophages was significantly decreased by 100 µM lutein 5,6-epoxide compared to the vehicle-treated control. The water-soluble form of lutein 5,6-epoxide-RAMEB decreases the activation of primary sensory neurons and macrophages, which opens perspectives for its analgesic and anti-inflammatory applications.

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